Chapter 11: Q60P (page 590)
The Williamson ether synthesis involves the displacement of an alkyl halide or tosylate by an alkoxide ion. Would the synthesis shown be possible by making a tosylate and displacing it? If so, show the sequence of reactions. If not, explain why not and show an alternative synthesis that would be more likely to work.
Short Answer
Step by step solution
About tosylate
The compound derived from tosyl chloride is tosylate.This compound is an ionic species and is represented by the symbol ‘Ts’. It is useful for organic synthesis for SN2 reactions.
About the reaction
The given reaction cannot proceed via SN2 reactions because there is a possibility of a backside attack due to the blockage of bridgehead carbon by the other bridgehead.
Another reason is the impossibility of bridgehead carbon to undergo inversion due to the constraints of the bridged ring system.
About the chemical reaction
The sketch of the chemical reaction is given below.
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